Chesterfield Travel Guide
Tourist Guide
Visit Chesterfield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.
Reviewed on 4 Nov 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
The price is NZ$172 per night from 7 Dec to 8 Dec
NZ$172
7 Dec - 8 Dec
includes taxes & fees
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,004 reviews)
The owner makes me feel like I am a personal friend of his and the best part of his day is when I walk in the door.
Reviewed on 7 Nov 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
The price is NZ$184 per night from 19 Nov to 20 Nov
NZ$184
19 Nov - 20 Nov
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (946 reviews)
Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned.
Reviewed on 8 Nov 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
The Clearing - Quiet - Close To Nature
Cummington
Stay at this cottage in Cummington. Enjoy free WiFi, private pools, and a garden. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (199 reviews)
Everything was amazing!
Reviewed on 20 Oct 2025
Peace and quiet on the lake
Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (227 reviews)
Great peaceful weekend in this beautiful home.
Reviewed on 31 Oct 2025
Amore Estate - beautiful room with many places to explore and relax in.
Lenox
Book a stay at this family-friendly vacation home in Lenox. Enjoy private pools, laundry facilities, and in-room jetted tubs. Popular attractions Tanglewood ...
9/10 Wonderful! (31 reviews)
Great stay
Reviewed on 8 Oct 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Chesterfield Gorge
Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.
Chesterfield Public Library
Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
Chesterfield Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
